1,8-Diamino-p-menthane

Base Information

• Chemical Name: 1,8-Diamino-p-menthane
• CAS No.: 80-52-4
• Deprecated CAS: 14720-04-8
• Molecular Formula: C10H22 N2
• Molecular Weight: 170.298
• European Community (EC) Number: 201-287-7,247-508-0,625-993-3
• NSC Number: 5612
• UN Number: 2810
• UNII: S583DR301G
• DSSTox Substance ID: DTXSID3021772,DTXSID601224807
• Nikkaji Number: J1.684.547G,J36.813J
• Wikidata: Q27288645
• ChEMBL ID: CHEMBL1533517
• Mol file: 80-52-4.mol

Synonyms:1,8-diamino-p-menthane;1,8-p-menthanediamine;4-(2-aminopropan-2-yl)-1-methylcyclohexan-1-amine;KIER-C3

Chemical Property of 1,8-Diamino-p-menthane

Chemical Property:

• Appearance/Colour: dark coloured liquid
• Vapor Pressure: 10 mm Hg ( 20 °C)
• Melting Point: ?45 °C(lit.)
• Refractive Index: n20/D 1.4805(lit.)
• Boiling Point: 107-126 °C10 mm Hg(lit.)
• PKA: 11.02±0.70(Predicted)
• Flash Point: 200 °F
• PSA: 52.04000
• Density: 0.914 g/mL at 25 °C(lit.)
• LogP: 3.03190
• Storage Temp.: 2-8°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 170.178298710
• Heavy Atom Count: 12
• Complexity: 155
• Transport DOT Label: Poison

Purity/Quality:

97% ^*data from raw suppliers

1,8-Diamino-p-menthane, mixture of cis and trans isomers technical grade, 85% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Strong irritant to eyes and skin, calls for eye protection.
• Hazard Codes: T
• Statements: 23/24/25-34
• Safety Statements: 26-27-28-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(CCC(CC1)C(C)(C)N)N
• General Description: 1,8-DIAMINO-P-MENTHANE is a chemical compound used as a precursor in the synthesis of alkylating β-blockers, specifically in the study of N-(bromoacetyl)-N'-[3-(o-allylphenoxy)-2-hydroxypropyl]-1,8-diamino-p-menthane (BAAM) isomers. It plays a role in the development of affinity labeling ligands for β-adrenoceptors, with certain configurations (e.g., 2-1 isomer) demonstrating high affinity and irreversible binding to these receptors in rat heart and lung tissues. The compound's structural features contribute to the pharmacological activity of its derivatives, making it relevant for biochemical and receptor-binding studies.

Technology Process of 1,8-Diamino-p-menthane

There total 18 articles about 1,8-Diamino-p-menthane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

terpin hydrate (80-53-5,89923-77-3) → 1,8-diamino-p-menthane (80-52-4)

Guidance literature:

With sulfuric acid; sodium isocyanate; In water; at 0 - 50 ℃; for 12h; Reagent/catalyst;

Reference yield:

N-(2-(4-acetamido-4-methylcyclohexyl)propan-2-yl)acetamide (64374-26-1) → 1,8-diamino-p-menthane (80-52-4)

Guidance literature:

With sodium hydroxide; In ethylene glycol; at 170 ℃; for 13h;

DOI:10.1021/acs.jafc.6b03977

Reference yield:

1,8-p-menthane di-n-pentaneamide → 1,8-diamino-p-menthane (80-52-4)

Guidance literature:

With sodium hydroxide; In ethylene glycol; for 13h; Reflux;

upstream raw materials:

hydrogen cyanide

terpineol

1,8-dinitro-p-menthane

limonene.

Downstream raw materials:

N,N'-dimethylene-p-menthane-1,8-diyldiamine

1,8-dinitro-p-menthane

p-menthane-1,8-diyl diisocyanate

1,8-p-menthane dibenzamide

Refernces

Alkylating β-blockers: Activity of isomeric bromoacetyl alprenolol menthanes

10.1021/jm00149a028

The research aimed to isolate, elucidate the structures of, and characterize the interactions of four isomers of N-(bromoacetyl)-N'-[3-(o-allylphenoxy)-2-hydroxypropyl]-1,8-diamino-p-menthane (BAAM) with β-adrenoceptors. The purpose was to understand their activity as alkylating β-blockers and their potential use in affinity labeling of β-adrenoceptors, which is a technique valuable for biochemical and physiological studies of these proteins. The study concluded that the isomer with the aromatic group on carbon 1 of p-menthane and with the 2 configuration (2-1) had the highest affinity for β-adrenoceptors in rat heart and lungs and acted as a ligand that binds irreversibly at the drug binding site of the receptor. Other isomers also showed affinity for the receptors, though with varying degrees of effectiveness and impact on receptor affinity. Key chemicals used in the process included 1,8-diamino-p-menthane, o-allylphenyl glycidyl ether, bromoacetyl bromide, and various solvents and reagents for the synthesis, purification, and testing of the isomers.